Chief of Staff

Role Description

This is not a job. It’s a masterclass. In two to three years in this role, you will have learned how to run a content business from the inside out. You’ll be in the room where decisions get made on deals, financing, creative direction, and company strategy. You will have a seat at the table for every major business decision and direct access to the most senior leaders in the company.

You’ll be supporting Chad Gutstein, who oversees all business, finance, legal, production and administrative operations at Terminal B TV. This is not a support role in the traditional sense. It’s an operator role, with real ownership and real stakes.

The Honest Version: This is a high-intensity position. Chad currently works long days, regularly into the early morning, and often on weekends. This role exists in part to change that; to distribute the load more effectively and give Chad the ability to prioritize more selectively. You will be expected to produce excellent work under pressure, on tight timelines, with ambiguous information.

The upside: you will have complete freedom in how, when, and where you work. No micromanagement. No office to report to. No one tracking your hours. We operate on a freedom-and-responsibility model.

What You’ll Do

• Executive & Operational Coordination
  • Serve as a force multiplier for the President, COO & CFO.
  • Own the operating cadence: reporting for weekly management meetings, monthly accounting reviews, and board memos.
  • Build and maintain dashboards and summary reports in collaboration with various teams.
  • Coordinate with Legal, Accounting, and Production on financial close and cash flow updates.
  • Act as a proxy for the President in internal and external communications.
• Financial Modeling & Strategic Planning
  • Develop and refine operational models in Excel/Google Sheets and Planful.
  • Support quarterly, annual, and long-range planning processes.
  • Partner with Accounting to validate actuals and support forecasting accuracy.
  • Assist in structuring and maintaining financial models for strategic initiatives.
• Communications & Reporting
  • Draft executive memos, board reporting packages, investor materials, and presentations.
  • Lead reporting design for KPIs and operational performance.
  • Coordinate the preparation of materials for lenders, investors, and board members.
• Cross-Functional Project Management
  • Oversee execution and follow-ups from high-level strategy meetings.
  • Lead or support ad hoc strategic projects.
  • Serve as a liaison between Finance, Legal, and Production.

What We’re Looking For

• 3–5+ years of experience in management consulting, investment banking, or a directly comparable field.
• Prior experience in content, media, technology, or entertainment is preferred but not required.
• A bachelor’s degree in any field.

Skills & Capabilities

• Financial modeling expertise: advanced Excel and Google Sheets skills.
• Communication excellence: ability to write clear and concise memos or decks.
• Presentation design: fluent in Canva, Google Slides, or other presentation software.
• AI fluency: use of tools like Claude, ChatGPT, and Gemini as work accelerators.
• Familiarity with Planful, QuickBooks, Slack, Ironclad, Zeck, Carta, Docusign, or other AI-enabled SaaS platforms is a bonus.

Who You Are

• Exceptionally organized.
• A strong communicator.
• A natural collaborator.
• Calm under pressure.
• Discreet and trustworthy.
• Genuinely curious.
• Entrepreneurially minded.
• A complement, not a copy.
• Kind, warm, caring & fun with a good sense of humor.

Compensation & Benefits

• Base Salary: $140,000 – $160,000 (dependent on experience and location).
• Performance Bonus: Annual, tied to company and individual performance.
• Work from wherever you are in the United States.
• Flexible schedule: manage your own time, own your results.
• Comprehensive medical, dental, vision, and life insurance coverage.
• Up to 10 days of paid sick leave per calendar year.
• No cap on vacation.

Equal Opportunity & Inclusion

Terminal B TV is an equal opportunity employer. We are committed to building a team that reflects the full breadth of human experience and do not discriminate on the basis of any characteristic protected by applicable law.